Unprotected Xylose-Derived Nitrone in Stereodivergent Synthesis of 4-Hydroxypiperidine Enantiomers: Weak Lewis Acid Induced Alteration of Stereochemistry in 1,3-Dipolar Cycloaddition

A one‐pot, two‐step synthesis of chiral 7‐oxa‐1‐azabicyclo[2.2.1]heptane derivatives from unprotected D‐xylose was achieved by an intramolecular 1,3‐dipolar cycloaddition of the N‐(γ‐alkenyl)‐substituted nitrone intermediate. The stereochemical course of the cycloaddition was altered by the addition...

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Published in:European journal of organic chemistry 2015-03, Vol.2015 (7), p.1533-1540
Main Authors: Rowicki, Tomasz, Malinowski, Maciej, Gryszel, Maciej, Czerwińska, Karolina, Madura, Izabela, Mironiuk-Puchalska, Ewa, Koszytkowska-Stawińska, Mariola, Sas, Wojciech
Format: Article
Language:English
Subjects:
Chiral pool
Cycloaddition
Imino­sugars
Lewis acids
Nitrogen heterocycles
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Summary:A one‐pot, two‐step synthesis of chiral 7‐oxa‐1‐azabicyclo[2.2.1]heptane derivatives from unprotected D‐xylose was achieved by an intramolecular 1,3‐dipolar cycloaddition of the N‐(γ‐alkenyl)‐substituted nitrone intermediate. The stereochemical course of the cycloaddition was altered by the addition of an achiral Lewis acid. The bicyclic byproducts were employed in a concise synthesis of two new enantiomeric piperidine‐type iminosugars. A one‐pot, two‐step synthesis of chiral 7‐oxa‐1‐azabicyclo[2.2.1]heptane derivatives from unprotected D‐xylose was achieved by an intramolecular 1,3‐dipolar cycloaddition of the N‐(γ‐alkenyl)‐substituted nitrone intermediate. The stereochemical course of the reaction was altered by the addition of an achiral Lewis acid. The bicyclic byproducts were used to prepare two new enantiomeric piperidine‐type iminosugars.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201403410